4-bromomethyl-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester | 784181-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-bromomethyl-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 4-bromomethyl-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate；ethyl 4-(bromomethyl)-1-(2-chlorophenyl)-5-(4-chlorophenyl)pyrazole-3-carboxylate
• CAS: 784181-20-0
• 化学式: C₁₉H₁₅BrCl₂N₂O₂
• 分子量: 454.15
• InChiKey: FZTPPZGJHFINES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromomethyl-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester 在 水 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 ethyl 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-hydroxymethyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  [EN] FUSED PYRAZOLE DERIVATIVES AS CANNABINOID RECEPTOR MODULATORS
  [FR] DÉRIVÉS DE PYRAZOLE CONDENSÉS EN TANT QUE MODULATEURS DU RÉCEPTEUR CANNABINOÏDE

  摘要：

  本发明涉及一种新型的大麻素受体调节剂，其化学式为(I)，特别是大麻素1（CB1）或大麻素2（CB2）受体调节剂，以及用于治疗由大麻素受体调节的疾病、症状和/或疾患（如疼痛、神经退行性疾病、进食障碍、体重减轻或控制以及肥胖症）的用途。

  公开号：

  WO2009095752A1
• 作为产物：
  描述：

  ethyl 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-1 H-pyrazole-3-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 生成 4-bromomethyl-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  [EN] CANNABINOID RECEPTOR MODULATORS
  [FR] MODULATEURS DU RÉCEPTEUR DE CANNABINOÏDES

  摘要：

  式(I)的化合物是大麻素受体CB1的调节剂，可用于治疗肥胖：式(I)。其中：X是一个键，或者从-C(R10)(R11)-*、-C(R10)(R11)-O-*、-C(R10)(R11)CH2-*、-C(R10)(R11)CH2-O-*、-CH2C(R10)(R11)-*、-CH2C(R10)(R11) -O-*中选择的二价基团。和-CH2-O-C(R10)(R11)-*，其中星号表示连接到吡唑环的键；Z是从指定组中选择的羧基异构基团；R3是氢、(C1-C)aIkyI或(C1C3)氟烷基；R4是式-(AIk1)P-(Q1)r(L)s-Q2的基团，其中p、r、s、AIk1、L、Q1和Q2如指定；或者R3和R4与它们连接的氮一起形成一个含有4至7个环原子的环氨基环，该环可选地被式-(L)s-Q2中的基团或上述定义的s、L和Q2定义的基团取代，或者通过一个可选的取代基团选择自羟基、甲氧基、-NH2-或单或双-(C1C3)烷基胺；R5、R6、R7和R8分别独立地选择自氢、-F、-Cl、-Br、-CN、(C1-C3)烷基、(C1C3)氟烷基、环丙基和-OR9；R10是氢、(C1C3)烷基、羟基或NH2，R11是氢或(C1-C3)烷基；或者R10和R11与它们连接的碳原子一起形成一个(C3-C5)环烷基环。

  公开号：

  WO2009074782A1

文献信息

• Cannabinoid receptor ligands and uses thereof
  申请人：Pfizer Inc

  公开号：US20040214855A1

  公开（公告）日：2004-10-28

  Compounds of Formula (I) and (II) that act as cannabinoid receptor ligands and their uses in the treatment of diseases linked to the mediation of the cannabinoid receptors in animals are described herein. 1

  本文描述了作为大麻素受体配体的化合物(I)和(II)的公式，以及它们在治疗与动物大麻素受体介导相关疾病中的用途。
• Acylaminobicyclic heteroaromatic compounds and uses thereof
  申请人：Dow L. Robert

  公开号：US20060241100A1

  公开（公告）日：2006-10-26

  Compounds of Formula (I) are described herein. The compounds have been shown to act as cannabinoid receptor ligands and are therefore useful in the treatment of diseases linked to the mediation of the cannabinoid receptors in animals.

  本文描述了式（I）化合物。已经证明这些化合物可以作为大麻素受体配体，并且因此在治疗与动物大麻素受体调节相关的疾病中很有用。
• Synthesis and structure–activity relationship of 1,2,4-triazole-containing diarylpyrazolyl carboxamide as CB1 cannabinoid receptor–ligand
  作者：Hee Jeong Seo、Min Ju Kim、Suk Ho Lee、Sung-Han Lee、Myung Eun Jung、Mi-Soon Kim、Kwangwoo Ahn、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmc.2009.12.040

  日期：2010.2

  Numerous research groups have been engaged in searching for novel CB1 receptor antagonists, since SR141716A (rimonabant), a CB1 receptor antagonist, proved to be efficacious in human for the treatment of obesity. In the present study, a series of 1,2,4-triazole-containing diarylpyrazolyl carboxamides based on the 1,5-diarylpyrazole template of rimonabant, was synthesized and tested for CB1 receptor binding affinity. The structure-activity relationship studies demonstrated that incorporation of 1,2,4-triazole ring onto the pyrazole scaffold via a methylene linker led to a significant improvement for CB1 receptor binding affinity. Importantly, these analogues also exhibited excellent selectivity for CB1 receptor over CB2 receptor. (C) 2009 Elsevier Ltd. All rights reserved.
• Exploring SAR features in diverse library of 4-cyanomethyl-pyrazole-3-carboxamides suitable for further elaborations as CB1 antagonists
  作者：Martin Cooper、Jean-Marie Receveur、Emelie Bjurling、Pia K. Nørregaard、Peter Aadal Nielsen、Niklas Sköld、Thomas Högberg

  DOI：10.1016/j.bmcl.2009.11.047

  日期：2010.1

  A chemically diverse library of secondary and tertiary 4-cyanomethyl-1,5-diphenyl-1H-pyrazole-3-carboxamides was synthesized to enable mapping of the SAR, in the eastern amide region, with regard to CB1 antagonist activity, This study was initiated as a prelude to the design and synthesis of possible CB1 antagonists that do not readily pass the blood-brain-barrier. In general a range of modi. cations were found to be tolerated in this part of the molecule, although polar and especially charged groups did to a degree reduce the CB1 antagonistic activity. Several compounds with single-digit or even sub-nanomolar potency, suitable for further elaboration of the nitrile moiety, were identified. (C) 2009 Elsevier Ltd. All rights reserved.
• WO2008/75012
  申请人：——

  公开号：——

  公开（公告）日：——